Woes of Being Beautiful
by Scarlett Rogue
Summary: The team needs a beautiful, blue-eyed brunette to go undercover and flirt their way into the heart of Jeffrey Montague, charity exploiter. Oh, and did they mention it had to be a guy? Should be easy for Neal Caffrey, right? Wrong. Mentions of slashness.
1. Next Case

**Summary: The team needs a beautiful, blue-eyed brunette to go undercover and flirt their way into the heart of Jeffrey Montague, charity exploiter. Oh, and did they mention it had to be a guy?**

**Rated: T  
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**This is a work in progress and may not be updated too frequently, so please be patient :) Thanks for reading, and reviews would be very lovely and inspiring.**

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Neal stood in front of the coffee machines early Monday morning, staring gloomily at the crust coating the insides of all the pots. Almost mournfully, he reached out slowly for the nearest pot, ready to pour himself a steaming mug of sludge and get to work on a hideously boring mortgage fraud case. His motions were cut off when a file was trust into his outstretched hand. Without a word he stuffed it under his arm and continued in his quest for crappy coffee.

"Morning, Peter. You're early."

"Yeah, well, I have to be. Hughes called me last night and said there was a serious case he needed us to work on. I spent three hours looking over the facts, and this one isn't gonna be easy."

"Are they ever?" Neal asked as the sludge poured into his cup. He added a bit of cream, something that he'd never done before coming to the Bureau; he learned quickly that black coffee in the outside world and black coffee at the Bureau were not the same things at all.

"Exploitation with an edge of violence. Lots of connections." Peter poured himself what was probably his second or third cup.

"Undercover?"

"You bet."

"Should be interesting. Conference room in five minutes?"

"Now we're talkin'." With that, Peter strode off toward his office to grab a few more files, Diana at his side with information of her own. Neal went back to his desk, closed the mortgage fraud case file, stashed it in the top drawer where he kept all unfinished cases, and headed up to the conference room. The usual team was starting to assemble and he took his seat toward the back, having the best view of the projector that was set up.

"Alright team, we have a very interesting and _very_ important case on our hands, and we'll need all the best people working on this in order for everything to go smoothly. One slip up and it's our asses, and possibly our lives." Peter stared into the eyes of his entire team, sans Neal. He just knew Neal was giving him the 'Negative Nancy' look.

Diana clicked the remote and an image of a man in about his early thirties popped up. His short blond hair was gelled back and his piercing green eyes held an aggressive glint to them. He seemed a bit boyish and harmless, but Neal knew better than to assume strength by appearance. Hell, Diana was living proof that you didn't need to be huge and muscular to scare the shit out of people.

"This is Jeffrey Montague, owner of a popular but hushed dance club in lower Manhattan called The Viper's Pit. He's been on police radar before, but only for smaller crimes. Unpaid parking tickets, having the police called on his parties one too many times, that sort of thing. He also runs a non-profit organization called New Horizon. It's an educational program for elementary-aged children. Basically, parents send their children to the after-school program for two months. If, after two months, they see good results, they agree to make a donation. This donation is _supposed _to go back to the school, used for new books, supplies, and technology for the children. All the employees are volunteer teachers so none of the money should, in theory, go anywhere but to the children."

"He was brought to _our _attention about a week ago when one of his employees at the club suspected him of using New Horizon's donations to fund an expansion on the club."

"Who's our inside guy?" Neal asked. Diana slapped another file in front of him, this one just one sheet of paper.

"Carlito Del Rossey, full-time bartender and Montague's go-to guy whenever the club is having issues."

"What kind of issues?" Jones asked, picking up the photo of the attractive hispanic man, no older than twenty-four.

"Competitive issues," Diana said. She clicked another button and the screen changed to a building Neal was familiar with. "Club Victory, located across the street from the Viper's Pit. Much more spacious. In the beginning this wasn't an issue, because Montague wanted the Pit to stay under the radar. In recent months his customers have been leaving to his competition because the popularity of the club was growing, but not the architecture. It became too crowded and people started to get aggressive."

"So Montague needs the donations from his organization to expand the club, so that customers aren't driven away anymore." Jones spoke down at a file.

"Precisely," Peter nodded.

"Alright, if we know this, what's the hold up?"

"We can't prove it."

The room was filled with silence and Neal shook his head. So it was going to be one of _those _cases, then.

"And that's where the undercover part comes in, I assume." Neal gestured to the folder and looked back up at Peter.

"We need someone to get the attention of Montague in a...romantic way."

"I hope this isn't one of those date-the-person-and-then-run-while-they-try-to-kill-you cases."

"Not exactly. See, Montague has been known to fall for a pretty face quite a bit. So we tempt him with just that, someone who few people can resist, and then hopefully gain his confidence. Then we can get whatever evidence we need to connect the organization's missing donations to Montague's club, and we can nail him."

Neal nodded and leaned on his hand, staring expectantly at Peter.

"Oh, yes, he has a type!" Peter jumped a little. Neal could tell he was excited about this case. Anything was better than a mortgage fraud, as long as lives weren't on the line.

"_That's_ what I was waiting for. I'm sure we have an agent somewhere around here who fits the bill."

"Oh, we do." Peter tried to hide his smile, for reasons unknown to Neal. Diana was definitely in on it, judging by the twitch of her lips. "He likes brunettes with blue eyes and unnatural beauty. And charm, of course."

"Excellent. Is there a racial preference?" Neal could tell Peter wasn't expecting that question.

"I don't believe so."

"Perfect! So we get Diana a pair of blue contacts and send her under."

Peter and Diana exchanged a look that Neal didn't quite understand.

"What? You said brunettes with unnatural beauty. I don't know about you, but I think Diana is _very _beautiful, and-"

"Caffrey, these are pictures of some of Montague's ex's." Diana slid another folder across the table and Neal opened it up immediately. The hand that had been absent-mindedly stroking his cheek fell onto the table with a loud thump and he stared at the pictures for a long few seconds before looking up.

"Or course, I should have known," Neal said. He smiled despite himself, entertained by how Peter and Diana had pulled this one over on him.

"Do you think it's possible?" Peter moved around the table to look down at the pictures with Neal-all brunettes, all with varying shades of blue eyes, and all beautiful beyond belief. Furthermore, _all male. _

"For me to flirt with guys?" Neal raised his eyebrows at Peter, who shrugged in response. "Peter, you wound me. I've got this in the bag! Consider this case closed."

"Alright," Peter said slowly, exchanging another look with Diana while Jones was smirking into his hand. "We'll set everything up. I want you back here in an hour on the dot to get wired up, understand?"

"Absolutely." Neal pulled his folders together and stood up, as did everyone else.

"And Neal-" The younger man spun around. "No anklet for this one," Peter said with a tilt of his head, a tilt that mean 'I'll be watching carefully'.

"Understood, Peter." Neal smiled his signature smile and left the room, heading toward the elevator. When he got outside he whipped his phone out and dialed a number without even thinking about it.

"Dare I say, problems with the Suit?" A voice answered, sounding amused.

"Moz, we have a problem. _I _have a problem."

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**Wow, this is actually pretty fun to write. Okay, I'm headed over to write the next chapter. Please review and tell me what you thought! **


	2. History

"Okay, just breathe, Neal. How much time do you have?" Mozzie asked, watching his friend pace back and forth in his room in June's home. Neal checked his watch for the tenth time since he got back.

"Thirty minutes. What am I gonna do, Moz?"

"Uh, you're gonna get wired, flirt with a man, and then stab him in the back." Mozzie gave him his face 'duh' expression. "Interesting how often the Suit complains about con artists lying, yet his entire career is based off lies."

"Yes, yes, the corruption of the bureaucracy. Moz, I can't _flirt _with a _man_."

"It wouldn't be the first time," Mozzie reminded him, head tipping sideways in a way that eerily reminded Neal of Peter.

"And we both know how well _that _ended."

"You were young, you didn't know what you were doing. But this is different. You understand people better. You understand _yourself _better."

"I just..." Neal fell on to the couch with a thump and buried his face in his hands. "I never wanted to think about that. Ever."

"What, did you think you could run from it forever?"

"I'm a pretty good runner," Neal waved him off.

"But Peter's better. I have to admire the suit; he has a way of making you confront your past without even trying." Neal shook his hair out and sighed, knowing that he had to make his way back to the office soon.

"What if _he's _there, Moz? The Viper was his place to relax. What if I bump into him and he blows my cover...and I fail Peter."

"It is impossible to live without failing at something, unless you live so cautiously that you might as well not have lived at all - in which case, you fail by default."

"Einstein?" Neal looked over at his friend.

"No, J.K. Rowling. Now go, before the suit comes here looking for you." Neal grabbed his jacket off the back of a chair and headed out slowly. He made his way to the office, walking a bit faster when he saw that he had ten minutes to get there, and thought about the current case.

There were many things about Neal's past that he wished to forget, but there was one thing this case refused to let him forget: Cory Lestrade.

Neal thought about Cory as he crossed the street in front of the huge office building. Cory was three years older than him, an inch shorter (last time he checked) and with the most beautiful smile Neal had ever seen on a man. Neal with eighteen when they met, alone in the world, and instantly drawn to the older man. With his dark curls and golden eyes, Cory was an unintentional heartbreaker for everyone. Well, everyone except Neal.

He and Neal began as friends, moved closer to slightly more than friends, and on a night when the two stayed up too late and drank a little too much, they became much more than just friends. Neal liked Cory a lot; he was brave, honest, and the most optimistic person he had ever known. He protected Neal when the boy had just moved to Manhattan and gave him a place to stay.

Their relationship was always on the rocks thanks to Neal. At that age he had already decided to start making new identities for himself, identities other than Neal Caffrey. Cory didn't like it, but he didn't tell Neal what to do. Problems arose when Neal's most important identity didn't fit with his lifestyle.

Neal Caffrey being his most important identity. When Neal first changed his name he wrote down a thorough list of characteristics that he wanted Neal to have. Charm, confidence, and motivation were only a few that he wrote down. He delved deeper and decided that Neal would be straight, for no other reason than that it was just easier. Neal would probably have many problems facing him, and aversion to his sexuality was not going to be one of them. He thought about this list late at night as he felt the heat of Cory's body against his back. He was diverging from his list. At the time, he had thought it was a huge problem.

In the end, it ruined everything. Neal felt that he had to stay strictly to the personality he had created, which included an intense attraction to women, but none to men. He had chosen to ignore what he knew now in favor of protecting the identity he had created. And he had pushed Cory away quickly after that.

Now, as Neal took the elevator up to his floor, he wondered how different his life would have been if he had told that little con man voice in the back of his head to shut the hell up and just be happy with Cory. Would they still be together? Would he have turned away from crime in favor of a better life?

He would never know, and that's what irked him the most. This case was already making his head hurt and it had barely begun.

"Punctual, Caffrey." Neal peaked down at his watch to see that it was exactly eleven.

"You know how much I hate to miss undercover work," Neal said with a smile. Instead of the familiar wires that he was expecting, Neal was presented with a beautiful, fake Rollex.

"By any chance do they have a bug scanner?"

"The club doesn't, but Montague might. If you make it back to his place, he might-"

"Woah, slow down there, Butch. Back to his place?"

"Yeah," Peter said casually. "You have to get his attention, Neal. Flirt with him, make him want you, which may lead to an invitation."

"As long as I don't have to sleep with him," Neal muttered.

"Well, you _might _need to cowboy up on this one," Peter said with a sly smile. The look on Neal's face earned him a hearty laugh.

"Alright, what's my cover?"

Peter handed him another folder and Neal flipped it open, filing the information away quickly.

"Nick Stanton, twenty-six years old, bartender and a close friend of Carlito."

"Twenty-six?" Neal raised a brow at Peter, who shrugged and patted him on the shoulder.

"You can pull it off."

"And Carlito's friend?"

"Montague trusts Carlito. He's his go-to guy. Now, all you have to do is ace your interview and show off those bartending skills I know you're hiding from me, and you'll get to meet Montague. From there..."

"The fun begins."

Diana came in to the conference room with an armful of clothes that she knew Neal would approve of: Pin-striped dress pants that hugged his bottom ever so slightly, a white button down shirt and a classy black vest and tie. Neal started to strip right there, leaving Peter wheeling around for the blinds as fast as he could and scolding Neal for public indecency. Diana laughed along with Neal at Peter's huffing until he was all dressed and ready to go. He slipped the watch on and clicked the button on the side, familiar with this handy device.

"Now, Neal, remember: If they try to scan you for bugs-"

"Click the button off, I know. Anything else?"

"Yes. You'd better make a damn good impression with Montague. The case-"

"Depends on it, _I know_."

"Fine." Peter stood in front of Neal, hands on hips, assessing him. "Jones, Diana and I will be right outside if anything goes wrong. Just say the word and we'll have backup there within minutes."

"Hmm...I wonder..." Neal said as the three agents and he left the building and made their way into the van.

"What?" Jones eyed him warily.

"Does your cover ever get blown because of the painfully obvious FBI van sitting _right _outside?"

"Surprisingly, no."

"Fascinating."

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**Thanks so much for your reviews for the first chapter! I'd love some for this, as well. More motivation for chapter 3! I'll get started on it right now, but really, your reviews determine how fast I post it :D  
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	3. Audition

**I'm SO SORRY for the long wait, guys! This chapter pissed me off, because I know exactly where this is going AFTER this part, but I was struggling with how to (interestingly) bridge the gap. I think I epically failed. I hate this chapter. It's boring. I'm sorry. Next one will be MUCH more interesting! **

**I've also gotten a little (a lot) addicted to BBC Sherlock, but I'll deff keep this fic in mind. I'm excited to write the few parts! Don't feel obligated to review this part; I know it's shit and won't be offended if nobody reviews it.**

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Neal looked around the club for about a minute, taking in the low ceiling and pillars spread throughout the relatively-small room. Everything was draped in red and gold satin, new age covered the walls (to Neal's dismay) and the center of the room held a small dance floor. Despite the tiny size, couples were wrapped around each other out on the dance floor, singles brushed up against each other, strangers touched without even realizing it. It was the mentality of familiarity, or being used to a lack of personal space.

These people were _not _going to be happy about this place possibly being shut down. Neal could tell by their behavior that they loved this club. They, at least, were loyal to the place.

"Welcome to the Viper's Pit!" A man Neal instantly recognized as Carlito stood in front of him, a bright and knowing smile plastered onto his face. "Would you, by any chance, be Nick Stanton?"

"That's me," Neal said with a smile of his own. He didn't miss the quiet relief that passed through the young Latino's eyes.

"Wonderful! My name is Carlito and I'm the head bartender here at the Pit. The assistant manager is waiting behind the bar to conduct your interview of sorts. Follow me." Carlito winked and turned around, heading to the bar in the further wall from the entrance. Neal followed at his own pace, peaking around at the people in the club. Some of them really _did _look hostile.

He figured all of the nicest customers must have gotten fed up with it and went over to Victory by this point.

"Mr. Clark, this is Nick Stanton, your interviewee. Nick, this is Kingsley Clark, assistant manager of the Pit."

"Pleasure to meet you, Mr. Clark." Neal shook hands with the white-haired man, who gave a tiny jerk of the head in response and waved a hand at Carlito. The younger man brought a few glasses forward and set them on the bar, along with a few random bottles. He then excused himself to assist customers.

"Alright Nick, what you have to do is simple: I give you a drink, you mix it up for me." Neal nodded a smiled, silently thanking Mozzie for giving him a crash course last night on some of the drinks he was less familiar with- particularly the comes contained beer.

After six different drink mixes, Neal was feeling confident and good about his work. Per usual when he was undercover, he started to feel like he belonged in this business.

"I think you'll be just fine here, Nick. Why don't you take the day off while I get your schedule ready? I'll give you a call later today with your hours."

"Thank you, Mr. Clark. And...will I be meeting the owner soon?" Neal asked casually, placing a few bottles back where they belonged. Across the bar, Carlito gave him a small, conspiratorial smile.

"You'll probably meet him on your first day. Don't worry about that, now. Why don't you hang around for a bit and become acquainted with the club?" With another wave of his hand, Neal found himself out on the floor once more. He nodded to the man and walked a ways away, headed for the door. He didn't want to stay in this club anymore than absolutely necessary.

"See, wasn't so bad, was it?" Peter said when Neal climbed into the van, which had driven one street over to pick him up.

"Not yet."

"Relax, Neal. It's like a dance!"

"I thought there was no dancing for me?" Neal grinned and Peter pushed him lightly on the shoulder, remembering one of the first conversations they had when Neal got out of prison.

"Good point. And Montague isn't exactly on your dance card..."

Neal shook his head and hid his grin. If only Peter knew how wrong he was. Though, Neal doubted he'd ever actually be attracted to a man like Montague.

The van slowly rolled passed the club and Neil peaked out the back window. His eyes fell on a man who looked oddly familiar, but when he looked again the man was gone. He shook his head, pushing away the image that was trying to sidetrack him. It would do him no good to become emotionally compromised by this case, not for a man he hadn't seen in fourteen years.

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**I'll have the next chapter up asap, guys! Sorry for the wait!**


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